35. "Teardrops on My Guitar" (2006)
One of her defining early smashes – and the one that marked her crucial crossover to the minivan-mom adult audience, where country stars do most of their business. It also inspired the first anti-Taylor answer song – Joe Jonas sang, "I'm done with superstars/And all the tears on her guitar" in 2009, on the JoBros' instantly forgotten Lines, Vines and Trying Times.
Best line: "Drew walks by me/Can he tell that I can't breathe?"